Rh2(OAc)4催化的Wittig-Type烯基化反应: 一种合成烷基、芳基取代的亚烷基丙二酸酯的简便方法

doi:10.6023/cjoc201902036

有机化学 ›› 2019, Vol. 39 ›› Issue (8): 2328-2332.DOI: 10.6023/cjoc201902036 上一篇下一篇

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Rh₂(OAc)₄催化的Wittig-Type烯基化反应: 一种合成烷基、芳基取代的亚烷基丙二酸酯的简便方法

邓超^†,a,b, 周姣龙^†,*,a, 刘华魁^a, 王丽佳^*,c, 唐勇^a

^a中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
^b南京农业大学理学院江苏省农药学重点实验室南京 210095
^c华东师范大学化学与分子工程学院上海 200241

收稿日期:2019-02-28 修回日期:2019-04-12 发布日期:2020-05-08

Rh₂(OAc)₄Catalyzed Wittig-Type Olefination: A Facile Access to Alkylidene and Arylidene Malonates

Deng Chao^†,a,b, Zhou Jiaolong^†,*,a, Liu Huakui^a, Wang Lijia^*,c, Tang Yong^a

^aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
^bJiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095
^cSchool of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241

Received:2019-02-28 Revised:2019-04-12 Published:2020-05-08
Contact: * E-mail: ljwang@chem.ecnu.edu.cn; jolorsh@sioc.ac.cn

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摘要/Abstract

发展了一种羰基化合物与重氮丙二酸二甲酯在三苯基砷和催化量的Rh₂(OAc)₄作用下发生一锅反应, 合成芳基、烷基取代的亚烷基丙二酸酯的新方法. 该方法的底物范围很广, 包括芳香醛和脂肪醛以及酮等羰基化合物, 都能够顺利地进行反应, 得到中等至优良的收率(59%~99%). 在0.5 mol%的铑催化剂作用下, 能够实现克级反应. 初步的机理研究表明, 这一烯烃化反应是通过铑-卡宾转化为砷叶立德的途径实现的.

In the presence of triphenylarsine and catalytic amount of Rh₂(OAc)₄, one pot reactions with carbonyl compounds and dimethyl diazomalonate give the corresponding alkylidene and arylidene malonates in moderate to excellent yields (59%~99%). The scope of the carbonyl compounds covered a broad range, including aromatic and aliphatic aldehydes and ketone. The reaction was easily scaled up to gram scale with 0.5 mol% rhodium catalyst loading. The preliminary mechanistic studies showed that the olefination proceeded via a rhodium-carbene transformed arsonium ylide pathway.

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邓超, 周姣龙, 刘华魁, 王丽佳, 唐勇. Rh₂(OAc)₄催化的Wittig-Type烯基化反应: 一种合成烷基、芳基取代的亚烷基丙二酸酯的简便方法[J]. 有机化学, 2019, 39(8): 2328-2332.

Deng Chao, Zhou Jiaolong, Liu Huakui, Wang Lijia, Tang Yong. Rh₂(OAc)₄Catalyzed Wittig-Type Olefination: A Facile Access to Alkylidene and Arylidene Malonates[J]. Chinese Journal of Organic Chemistry, 2019, 39(8): 2328-2332.

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Rh₂(OAc)₄催化的Wittig-Type烯基化反应: 一种合成烷基、芳基取代的亚烷基丙二酸酯的简便方法

Rh₂(OAc)₄Catalyzed Wittig-Type Olefination: A Facile Access to Alkylidene and Arylidene Malonates

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